Best Hotels in Town of Southold Town for 2025

Our customers tell us that they can't get enough of the helpful staff at Silver Sands Motel & Beach Bungalows. During your stay, you'll be within walking distance of Railroad Museum of Long Island. Features include free WiFi in public areas and free self-parking, plus 2 restaurants.

Our customers tell us that they can't get enough of the helpful staff at The Harbor Front Inn. During your stay, you're just a quick walk from Camera Obscura. Enjoy features like free breakfast, plus a 24-hour gym and concierge services.

Our customers tell us that they can't get enough of the helpful staff at Greenporter Hotel. During your stay, you're just a quick walk from Railroad Museum of Long Island. Enjoy features like free WiFi in public areas and free self-parking, plus a 24-hour gym.

Our customers tell us that they can't get enough of the helpful staff at Sound View Greenport. During your stay, you'll be close to East End Seaport Maritime Museum. Features include free breakfast and free WiFi in public areas, plus 2 bars.

Our customers tell us that they can't get enough of the helpful staff at The Shoals Suites and Slips. During your stay, you're just a quick walk from The Old Field Vineyards. Enjoy features like a restaurant, a bar and a coffee shop/cafe.

During your stay at Cliffside Resort Condominiums, you'll be close to Railroad Museum of Long Island. Enjoy features like free WiFi in public areas and free self-parking, plus laundry facilities. This comfortable aparthotel has 68 apartments over 2 floors. Each apartment includes amenities such as free WiFi and a kitchenette.

Our customers tell us that they can't get enough of the helpful staff at The Menhaden. During your stay, you're just a quick walk from Camera Obscura. Free breakfast, free WiFi in public areas and a restaurant are available.

During your stay at Hotel Moraine, you'll be close to Greenport Carousel. You'll find features such as free breakfast and free self-parking, plus a restaurant.

Our customers tell us that they can't get enough of the helpful staff at American Beech Hotel. During your stay, you're just a quick walk from Greenport Farmers' Market. Enjoy features like free breakfast and free WiFi in public areas, plus a restaurant. This property offers pet-friendly amenities, such as food and water bowls.

During your stay at this villa, you're just a quick walk from Orient By The Sea Marina. Enjoy features like an outdoor pool and laundry facilities. Enjoy your stay with amenities like a private pool and a kitchen in the villa.

During your stay at this apartment building, you're just a quick walk from Railroad Museum of Long Island. Enjoy features like laundry facilities. Enjoy your stay with amenities like a washing machine in the apartment.

During your stay at Vine & Sand, you're just a quick walk from Corey Creek Winery. Features include free breakfast, free WiFi in public areas and free self-parking.

During your stay at this holiday home, you'll be within walking distance of Kontokosta Winery. You'll find features such as a gym and laundry facilities. A private pool and a kitchen are available in the holiday home.

During your stay at this holiday home, you'll be close to The Old Field Vineyards. You'll find features such as a water park, laundry facilities and an arcade/games room. Free WiFi and a kitchen are available in the holiday home.

During your stay at this holiday home, you're just a quick walk from Railroad Museum of Long Island. Features include laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.